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Orland Holiday Rentals

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50 rentals in Orland.
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Awanadjo Shores on Toddy Pond, holiday rental in Orland

Awanadjo Shores on Toddy Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake-side Living at Its Best on Toddy Pond, holiday rental in Orland

Lake-side Living at Its Best on Toddy Pond

3 bedrooms
3 bathrooms
Sleeps 6
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Upscale Waterfront Cedar Log Cabin, holiday rental in Orland

Upscale Waterfront Cedar Log Cabin

3 bedrooms
2 bathrooms
Sleeps 6
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The Riverhouse, holiday rental in Orland

The Riverhouse

2 bedrooms
1 bathroom
Sleeps 4
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Private 2-Story Cottage with Lake View on 7 Acres, holiday rental in Orland

Private 2-Story Cottage with Lake View on 7 Acres

3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront shingled cottage w/ shared boat dock - near Acadia!, holiday rental in Orland

Waterfront shingled cottage w/ shared boat dock - near Acadia!

1 bedroom
1 bathroom
Sleeps 2
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Updated lakefront cottage w/ shared grill & boat dock - near Acadia, holiday rental in Orland

Updated lakefront cottage w/ shared grill & boat dock - near Acadia

1 bedroom
1 bathroom
Sleeps 2
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Vacation Home with private lake frontage- Great Summer or Fall Getaway!!, holiday rental in Orland

Vacation Home with private lake frontage- Great Summer or Fall Getaway!!

2 bedrooms
1 bathroom
Sleeps 4
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New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!, holiday rental in Orland

New to VRBO! Private Beach, Beautiful Cottage, Minutes to Castine. Maine Heaven!

3 bedrooms
1 bathroom
Sleeps 6
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Peaceful location perfect for couples or small family, holiday rental in Orland

Peaceful location perfect for couples or small family

2 bedrooms
2 bathrooms
Sleeps 4
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A perfect place for a couples getaway!  Picturesque Lakefront cottage., holiday rental in Orland

A perfect place for a couples getaway! Picturesque Lakefront cottage.

1 bedroom
2 bathrooms
Sleeps 2
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Peaceful Seaside Escape on Spectacular Penobscot Bay, holiday rental in Orland

Peaceful Seaside Escape on Spectacular Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 6
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The Brick House in the Woods...A Four-Season Retreat! Room for a large family!, holiday rental in Orland

The Brick House in the Woods...A Four-Season Retreat! Room for a large family!

4 bedrooms
2 bathrooms
Sleeps 12
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Peace and Tranquility on Private Pierces Pond, holiday rental in Orland

Peace and Tranquility on Private Pierces Pond

4 bedrooms
3 bathrooms
Sleeps 8
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Serene Lakefront Cabin on Beautiful Spring Fed Pond - Close to Acadia and MDI, holiday rental in Orland

Serene Lakefront Cabin on Beautiful Spring Fed Pond - Close to Acadia and MDI

3 bedrooms
1 bathroom
Sleeps 6
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Luxurious Lake Camp! Close to Bar Harbor and Acadia Nt'l Park, holiday rental in Orland

Luxurious Lake Camp! Close to Bar Harbor and Acadia Nt'l Park

3 bedrooms
2 bathrooms
Sleeps 8
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Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings   5 star, holiday rental in Orland

Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings 5 star

7 bedrooms
3 bathrooms
Sleeps 21
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Beautiful, Private Oceanfront Cottage on Penobscot Bay, holiday rental in Orland

Beautiful, Private Oceanfront Cottage on Penobscot Bay

3 bedrooms
2 bathrooms
Sleeps 6
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WATERFRONT home on pristine Maine Lake; FAMILY FRIENDLY!, holiday rental in Orland

WATERFRONT home on pristine Maine Lake; FAMILY FRIENDLY!

7 bedrooms
3 bathrooms
Sleeps 16
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Bangor Acadia Furnished Tiny House, Short/Long Term, Medical Traveling, Holidays, holiday rental in Orland

Bangor Acadia Furnished Tiny House, Short/Long Term, Medical Traveling, Holidays

1 bedroom
1 bathroom
Sleeps 4
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Charming Sandy Point Home, holiday rental in Orland

Charming Sandy Point Home

4 bedrooms
3 bathrooms
Sleeps 10
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Original Lucerne-in-Maine cabin, holiday rental in Orland

Original Lucerne-in-Maine cabin

2 bedrooms
1 bathroom
Sleeps 6
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Secluded  Lakefront Home Minutes from Bangor., holiday rental in Orland

Secluded Lakefront Home Minutes from Bangor.

3 bedrooms
1 bathroom
Sleeps 8
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Modern Water's Edge Home, holiday rental in Orland

Modern Water's Edge Home

3 bedrooms
2 bathrooms
Sleeps 8
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Relax And Sleep In The Trees While Listening To The Loons Call On Phillips Lake, holiday rental in Orland

Relax And Sleep In The Trees While Listening To The Loons Call On Phillips Lake

2 bedrooms
2 bathrooms
Sleeps 7
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4 Bedroom/2.5 Bath Right On The Penobscot Bay And Close To Acadia.  Dog Friendly, holiday rental in Orland

4 Bedroom/2.5 Bath Right On The Penobscot Bay And Close To Acadia. Dog Friendly

4 bedrooms
3 bathrooms
Sleeps 8
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Seacroft, holiday rental in Orland

Seacroft

1 bedroom
1 bathroom
Sleeps 2
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Colcord Cottage- quintessential oceanfront cottage, holiday rental in Orland

Colcord Cottage- quintessential oceanfront cottage

2 bedrooms
1 bathroom
Sleeps 6
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Beautiful  cottage in the woods on pristine  Branch Lake, Ellsworth ME, holiday rental in Orland

Beautiful cottage in the woods on pristine Branch Lake, Ellsworth ME

3 bedrooms
2 bathrooms
Sleeps 7
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Spacious Four Season House on Phillips Lake, holiday rental in Orland

Spacious Four Season House on Phillips Lake

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Maine. Lovely Cottage on Penobscot Bay, holiday rental in Orland

Maine. Lovely Cottage on Penobscot Bay

3 bedrooms
1 bathroom
Sleeps 6
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Vacation in affordable luxury!  Scenic, private, quiet. May & June now open!, holiday rental in Orland

Vacation in affordable luxury! Scenic, private, quiet. May & June now open!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Your Maine Retreat' is a unique, one of a kind experience., holiday rental in Orland

'Your Maine Retreat' is a unique, one of a kind experience.

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Log Cabin on Beautiful Phillips Lake near Bar Harbor and Camden, holiday rental in Orland

Cozy Log Cabin on Beautiful Phillips Lake near Bar Harbor and Camden

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Bayside Retreat On Penobscot Bay:  Perfect Midcoast/DownEast Location!, holiday rental in Orland

Private Bayside Retreat On Penobscot Bay: Perfect Midcoast/DownEast Location!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tranquility on Penobscot Bay Private Retreat: Perfect Midcoast/DownEast Location, holiday rental in Orland

Tranquility on Penobscot Bay Private Retreat: Perfect Midcoast/DownEast Location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful lake house for 12 in Holden, miles of hiking and technical bike trails, holiday rental in Orland

Beautiful lake house for 12 in Holden, miles of hiking and technical bike trails

3 bedrooms
2 bathrooms
Sleeps 12
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A cozy cabin just 20 feet from the shore of Toddy Pond, holiday rental in Orland

A cozy cabin just 20 feet from the shore of Toddy Pond

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Steamboat Crossing Cabins: #2 Maple Cabin, holiday rental in Orland

Steamboat Crossing Cabins: #2 Maple Cabin

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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We now have heat pump...like A/C!! Lakefront, mountain biking and hiking trails!, holiday rental in Orland

We now have heat pump...like A/C!! Lakefront, mountain biking and hiking trails!

1 bedroom
1 bathroom
Sleeps 8
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The Hollyhock House, holiday rental in Orland

The Hollyhock House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Sandy Point Getaway w/ Wraparound Deck!, holiday rental in Orland

Beautiful Sandy Point Getaway w/ Wraparound Deck!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rustic Searsport Cabin: Loft + Sunroom on 10 Acres, holiday rental in Orland

Rustic Searsport Cabin: Loft + Sunroom on 10 Acres

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Maine. Lovely Tiny House on Penobscot Bay, holiday rental in Orland

Maine. Lovely Tiny House on Penobscot Bay

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Sea Captain's Cottage 5 minutes from sea., holiday rental in Orland

Luxury Sea Captain's Cottage 5 minutes from sea.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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'Eagles Nest' Mountain Retreat with 250 mile views on way to Acadia, holiday rental in Orland

'Eagles Nest' Mountain Retreat with 250 mile views on way to Acadia

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Maine Vibes Farm, holiday rental in Orland

Tentrr Signature Site - Maine Vibes Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Family Friendly, Waterfront Home near Castine, Maine, holiday rental in Orland

Family Friendly, Waterfront Home near Castine, Maine

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sandy Point Brook side Coastal Cottage- Easy Shores, holiday rental in Orland

Sandy Point Brook side Coastal Cottage- Easy Shores

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Brand new farm cottage close to downtown Blue Hill and Acadia National Park, holiday rental in Orland

Brand new farm cottage close to downtown Blue Hill and Acadia National Park

1 bedroom
1 bathroom
Sleeps 2
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